Acetone, oxime → 3-[2-(Diethyloxymethyl)-benzoyl]-2-[((isopropylidene)amino]oxy]-pyridine

HRID 1422152Notes

Reaction equation

HRID 1422152 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].F[C:13]1[C:18]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[O:20])=[CH:17][CH:16]=[CH:15][N:14]=1>O1CCCC1>[CH2:32]([O:31][CH:27]([O:28][CH2:29][CH3:30])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:19]([C:18]1[C:13]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])=[N:14][CH:15]=[CH:16][CH:17]=1)=[O:20])[CH3:33]

Participants

5

Reactant 3

HCID 67180Acetone, oximeHCID 18357614(2-Fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 183576123-[2-(Diethyloxymethyl)-benzoyl]-2-[((isopropylidene)amino]oxy]-pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.49 g of acetone oxime in 8 ml of dry tetrahydrofuran was added 0.75 g of potassium tert-butoxide. The solution was stirred for 15 min. then a solution of 1.86 g of (2-fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanone in 8 ml of tetrahydrofuran was added. The solution was stirred at room temperature for 30 min. then quenched by the addition of 25 ml of a 1:1 water-saturated ammonium chloride solution. The solution was extracted with two 50 ml portions of ether and the combined ether extracts were washed with brine and dried over sodium sulfate. Evaporation afforded the intermediate 3-[2-(diethyloxymethyl)-benzoyl]-2-[((isopropylidene)amino]oxy]-pyridine which was not characterised but dissolved in 30 ml of ethanol and 20 ml of 2 M hydrochloric acid added and the solution refluxed for 15 min. The solution was cooled to room temperature and the crystals of 2-(isoxazolo[5,4-b]pyridin-3-yl)-benzaldehyde were collected by filtration and dried in vacuo, 1H-NMR (200 MHz, CDCl3) d 10.26 (CHO).

Workup

  1. stirringThe solution was stirred at room temperature for 30 min.
  2. customthen quenched by the addition of 25 ml of a 1:1 water-saturated ammonium chloride solution
  3. extractionThe solution was extracted with two 50 ml portions of ether
  4. washthe combined ether extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customEvaporation

Sources & evidence

ORD record
ord-669892d971a44b4bb04401f8121ceaae
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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